First Times
by OldNarnian
Summary: Growing up with only a gruff dad, a useless older brother and no steady friends or family, Sam Winchester is next to clueless about girls. When he moves in with Jess, he's surprised when the life isn't perfect. He stumbles and blunders his way through a whole bunch of firsts with her, including an embarrassing trip to the drugstore for tampons.
1. Chapter 1

Buying Tampons

Sam walked alone on the small strip of sidewalk, a heavy textbook balanced open in one of his giant hands and his battered book bag in the other as he weaved through the milling crowd of students.

He didn't look up once as he sidestepped past giggling girls or yelling guys, his soft eyes slowly moving back and forth across the page, his red lips moving slightly as he tried to concentrate on the paragraph in front of him.

The harsh wind blew, causing the pages to flap and turn on their own before he was ready. Sam cursed the windy autumn day quietly as he flipped the book shut. It's not like the book was making any sense to him anyways.

Shoving the book in his bag and slinging it over his shoulder, he ducked behind another group of girls to walk up the short flight of stairs into the dorm room he now shared with his girlfriend, Jess.

They had been living together for two months now and it had been the best two months of Sam's short life.

Finally getting used to collage life, and feeling freer than ever before, he finally had someone to share his success and pleasures with. It didn't feel as lonely anymore. Plus, Jess was experimenting with cooking and it almost always turned out beautifully.

He walked in the door, ducking his head so he didn't hit it on the small doorframe, and set his bag down on the coffee table.

"Jess?" He called out.

Her last class of the day was finished twenty minutes before his, but Jess was a social butterfly, if Sam ever had seen one, and she was out with friends already a lot of the time before he got home.

"Sam?" She answered.

Her voice was taunt and cautious.

Sam's dark eyebrows pulled together in a knot immediately. Concerned, he went into the dimly lit bedroom they shared.

The smart outfit she had been wearing that morning was flung carelessly across the unmade bed sheets and her book bag was laying on its side on the ground, books spilling out onto the hardwood floor.

"Babe? You okay?" Sam knocked on the bathroom door where he could hear the water running.

The water shut off.

"Sam? How much do you love me?" Came Jess' small voice again.

"I love you a crazy, insane amount… why?" Sam asked.

He tried the door handle but it was locked.

"Okay… will you do something for me?"

"Anything you need."

Sam was now really concerned and he considered kicking the door in the lock clicked and Jess stepped out. Her hair was pulled into a messy bun at the back of her head, blond curls escaping everywhere.

The concern almost disappeared as Sam took in her appearance, she was wearing one of his tee-shirts and a pair of sweat pants. The kind that had giant legs but stopped and had a small band right below the knee.

She blushed under his gaze and tried to step back again but was stopped by the boyish grin that escaped onto Sam's lips.

"You're adorable." He said finally.

"Shut up!" She whined. Pushing past him, she went and sat on the bed and pulled her knees up ho her chest.

"Sorry!" Sam apologized, still grinning. "What's wrong? What do you need me to do?"

Jess sighed. "Do you want good news or bad news first?" She asked finally.

"Um, good?" Sam asked uncertainly. He awkwardly shifted his weight from foot to foot, not sure if he should go sit with her on the bed or just stand there some more.

"I'm not pregnant." Jess declared.

"Oh…" Sam blinked at her. "Um…"

"Bad news is I got my period in the middle of class and I don't have any tampons left."

Sam's heart started sinking. He was completely at a loss and it was terrifying him.

He felt like a sailor out alone on the stormy sea at night, with no one around to throw him a lifeline. He could handle a lot of things and take a lot of crap in a stride, but girl problems were not one of them.

"Congratulations?" He offered.

"Shut up." She said again. "Anyway, I just need you to run to the store and buy me a box of tampons." She looked up at his with her big blue eyes and stuck out her lower lip just the tiniest bit. "Please? It would really mean a lot to me."

Sam bit his lip hesitantly.

Growing up with only his dad and brother to talk to, he hardly knew what a tampon was, let alone how to buy one.

His stomach was churning uncertainly at the prospect of this challenge.

"Okay…" He agreed, surprising himself. "I guess I could… but I don't know what kind to get… _are _there different kinds?" He asked, suddenly horrified he'd said the wrong thing.

Jess rolled her eyes. "Of course there are different brands! And if you get the wrong one, I will cry at you." She tried to glare at him but ended up laughing at his fear stricken face.

"There's an empty box in the bathroom garbage. Just get the one that looks exactly like it."

She pointed to the bathroom and Sam had no choice but to follow her finger like a dog that had been kicked to retrieve the box from the garbage can.

He picked it up and gazed at it sadly. He had seen in under the sink but hadn't actually looked at it before.

It was purple and had white flowers plastered all over it. Easy.

"Okay, I'll be back in a few."

"Thanks, babe." Jess grimaced at him, her arms wrapped around her middle.

Sam glared at her as he picked up his keys and walked out the door. He shut the door gently and started jogging down the street, still dodging the huge body of students who seem ever-present on the streets.

He pulled his jacket closer as the wind picked up. Shaggy hair flying and eyes watering against the dusty wind, he pressed on to the nearest drugstore.

When he walked in, he kept his head down and tried to look small and not get himself noticed, a skill her never really had, and went to the aisle he had never before entered.

He thanked God it was empty as he started searching the shelves for the box like Jess had.

Fairly soon, he realized that it was not such an easy task, his eyes racked the long shelves and he still couldn't find the right box.

Some were pink and blue and some had stripes on them. Some said 'extra strength' and some said 'delicate' and some weren't even tampons but weird pads with wings on them.

A pretty girl ducked into the aisle and Sam blushed when he saw her and immediately wished he could be swallowed up by the ground.

The girl also look uncomfortable to find a tall, young, handsome man in the aisle with tampons but she only raised her eyebrow at him before grabbing the box she wanted.

She noticed how awkward the guy looked and offered him a small, cheeky smile. "How's the Mrs.?" She asked.

Sam blushed even darker and ducked his head down. "Uh, my girlfriend…. She just needs… and I said-"

The girl laughed. "You're doing great," she encouraged. "My boyfriend won't buy me tampons." She winked and then turned and quickly left, leaving a heavily blushing Sam in her wake.

While still on the search, another guy, about the same age as Sam, with light, shaggy hair and a slim build walked up the aisle.

He didn't look as out-of-place as Sam, but he looked just as unhappy about the unfortunate situation that had befallen the two of them.

Without too much hesitation, he grabbed one of the boxes that had pads with wings on them and held them in his hands.

He nodded at Sam. "S'up." He greeted.

Sam nodded back, wishing he would leave or stop acknowledging him.

The guy grinned sadly. "First time?" He asked, gesturing to the shelves behind him.

Sam nodded again. "Yeah, I just moved in with my girlfriend and now I guess this is a requirement for me."

The guy laughed. "Better get used to it now. You'll be doing this for the rest of your life."

He turned to leave but Sam stopped him.

"Hey, wait." He called. "Could you help me? Please?"

The guy turned again and narrowed his eyes as he looked Sam up and down, like he was sizing him up.

"Fine." He agreed, grudgingly. "But only this one time! It's bad enough I have to do it for my own girlfriend." He sighed, defeated. "What kind does she use? You have to know that or else she'll bite your head off."

"Uh, the box was purple… and it had these white flowers on it." Sam struggled to remember something else about it.

The guy reached up to the top shelf and pulled a box down and tossed it to Sam, who caught it and looked in wonder.

"Yeah! This is it." He breathed a sigh of relief. "Thanks, man."

The guy pointed a finger and glared at Sam. "Don't you _breathe_ a _word _of this to _anyone_."

Sam held up the box of tampons and raised one eyebrow. "Yeah… like I'll be doing that."

"Word of advice, chocolate works wonders."

And then he was gone.

Sam pondered the guy's words as he quickly left the aisle before another person walked in on him.

He sprinted to the frozen foods section and grabbed a tub of Jess' favourite ice cream, Oreo ice cream, before bolting to the checkout.

A sleazy looking guy at the check-out counter looked at the items Sam placed on the counter before scanning them in.

"That time of month again?" He asked, his lips curling into a sneer but was silenced by the most terrifying glare Sam could muster up.

The guy faltered and diverted his gaze.

"14.87$ is your total." He grumbled.

Sam paid him silently and then took his bag and walked away with as much dignity as he could find inside of himself.

He felt like every eye was on him as he walked down the street again. It felt like all the eyes could see into the bag he was carrying. Everyone seemed to be judging him and he had no idea why.

In reality, nobody gave his shopping bag a second glance, they were too distracted by the look of complete distress on the man's face as he power walked through the crowds.

When Sam's dorm room finally came into view, he started sprinting, just wanting the ordeal to be over.

Little did he know, he still had a week to go.


	2. Chapter 2

Buying Tampons

"Jess?" Sam called softly as he walked into their dorm room. The whole room, as far as he could tell, was plunged in as much darkness as possible.

He flicked on one of the big lights and went to put the ice cream in the freezer. He called out again. "Jess? You here?"

"I'm in the bathroom!" She yelled back. "Did you get the tampons?"

"Yeah, I got 'em." Sam made a face when he realized how whipped he sounded, he walked into their tiny bedroom and tried the bathroom door. It was locked.

"Jess, you gotta unlock the door if you want me to give them to you." Sam chuckled lightly. "Don't tell me you've forgotten how to do that."

The lock clicked and the door swung open.

"Stop being so annoying!" Jess yelled at him. She grabbed the bag from him and the slammed the door shut.

Sam rolled his eyes at the door, he wanted to protest her acting like this, like he used to with his dad, but something held him back.

He was surprised to find it was fear.

"Babe?" Jess' watery voice came from the bathroom. "Could you please make me some tea?" She sounded completely different from the girl that had slammed the door in his face seconds before.

"Sure… I can do that."

"Thanks…. I love you."

Bewildered, Sam went to the kitchen to make some of Jess' favourite tea.

As he waited for the kettle to boil, his thoughts slipped, unwanted, to all the times he had fought with his dad.

It had been a long time since he had been afraid of his dad. All he could really do to Sam, was hit him. His dad had lost the ability to hurt him emotionally a long time ago, when Sam first set his mind on leaving and closed off any other feelings.

He could remember the exact moment, it had felt like he was in a wind tunnel and he couldn't catch his breath because he knew that the life his dad and brother lived, was not going to be the life for him.

At that time, he didn't even know what he wanted to do or go, but he knew that he could and that set him free.

So the pain of his dad's fist on his face, in his stomach, or his dad's belt on his back, was nothing.

The kettle started whistling, Sam shook himself awake from the dark thoughts of his past to make the tea.

He forced his thoughts to go to the paper he had to write the next day. A long, dusty paper on a topic that even he found boring.

Jess emerged from the bedroom and came into the kitchen, she had her arms crossed over her stomach and she walked slowly, slumped over. She looked so defeated that Sam wanted to pick her up and take care of her.

He went over to her and wrapped his arms around her, she didn't uncross her arms but she pressed into him, burying her face into his chest.

"You smell good." She mumbled.

His chest rumbled as he laughed softly at her.

He lead her over to the counter and sat her on a bar stool. He poured the tea into her mug and handed her the sugar.

One tea spoon of sugar was all she needed.

It made Sam smile when he knew that, one more thing he loved about her. She was so extraordinary in everything ordinary and it never ceased to amaze him.

"Why are you staring at me?" She asked, she took a sip her tea and sighed with contentment.

"I dunno…" Sam replied, still grinning at her. "Oh!" He remembered something and quickly went to the freezer. "I bought this, too. I know it's your favourite."

Jess looked at him and her eyes filled with tears. Her big, full lips quivered slightly and she blinked rapidly, but the tears still managed to slip out and fall onto her pale face.

Sam stood, completely at a loss of what to do.

"Why are you crying?" He asked finally.

"Because I love you, you idiot!" She wailed. She wiped the tears off her face but more kept coming, until they were all smeared and she sat there, sniffing and crying.

"I don't understand." Sam said carefully, as if one wrong move would turn the situation dire.

"I've been having such bad cramps all day and my head hurts and you went and bought me tampons and made me tea after I yelled, and then you even bought me ice cream and it's just what I wanted." She stopped to blow her nose. "You're the best boyfriend ever."

Sam blinked a few times. "Uh, thank you… I guess." He stopped to smile. "That was the longest sentence I've ever heard."

She laughed through her tears.

"I know… don't listen to me, I'm going crazy." She wiped away the last of her tears and took a deep breath. "Why don't you say we have ice cream for supper and watch movies until we pass out on the couch?" Jess asked.

"How about you eat ice cream for supper and I eat real food?" Sam asked.

"Sounds good to me." Jess' watery smile made Sam laugh again.

He leaned over the counter and kissed her nose.

"Go pick a movie and I'll make food for me and bring you your ice cream."

Jess nodded and hoped off the bar stool to go to the living room.

As Sam prepared his food, left over casserole from Jess' mom, he could only shake his head at the strangeness of women.

He grabbed a beer and went to sit with Jess. He moaned when he saw her choice, A Walk To Remember.

"Oh come on!" She defended herself. "It's a great movie!"

"Maybe for you." Sam grumbled. "I'm way to manly for it."

Jess rolled her eyes and tucked her head in the perfect little nook on his arm.

"But you're going to watch anyways because you love me."

Sam rolled his eyes and took a sip of his beer, yeah, he was going to watch it. But only because he loved her.

Jess spooned the ice cream into her mouth as she tried to not cry again at the movie and Sam sympathized deeply with Landon Carter, the main character as he struggled to not fall in love with the strangeness of Jamie.

"What if that was me?" Jess asked suddenly.

"Hhm?" Sam looked away from the movie. "What'd you say?"

I said, what would you do if that was me?" Jess asked again. "What would you do if I died?"

Sam's throat closed up and he had trouble talking/ "Don't." He managed. "Please, don't talk about it."

"No, seriously." Jess sat up and looked deeply into his eyes. "What would you do?"

Sam averted his gaze. "I guess it depends…" He said finally.

"On what?"

"On how you died…" Sam started picking at the label on his now empty beer. "If you died of cancer, I would give you the best damn funeral and honor your name forever… I'd probably drop out of school and start an organization that raised money for other cancer patients so nobody would have to endure the pain I was in. But if you were killed…"

He hesitated.

"What? What would you do?"

"I would hunt whoever did it down and kill them. I would… I avenge you."

Jess was quiet for a minute. "Both of those things involve you stopping your entire life." She said finally.

"Yeah? So?"

"Sam," Jess stroked his face. "If I die, whether I'm murdered or any other way, I want you to finish school and become a lawyer."

"But-"

She put her finger on his lips. "I'm not planning on dying anytime soon, it's okay. I'll stick around for a long time yet. But I'm just saying, if that happens, I want you to be happy. Finish school and find another girl, have a family. Don't stop your life, live it. Live it for me."

Sam kissed her. "Okay… just… don't die."

She smiled into the kiss. "I won't." She mumbled against his lips.

.,.,.,.,.,.

Sam pulled at the collar of his suit. It was uncomfortable and he would have hated it if he had energy to do anything other than stare blankly at the mound in the ground where Jess lay.

The hot day was buzzing and the smell of flowers was thick everywhere. And yet, Sam only stared.

_Finish school, find another girl, have a family._ Her voice said softly in his mind.

_It took her, It killed her. You have to make it understand the pain it caused you and make it feel that tenfold. _Another voice in his mind yelled, louder than Jess.

"I have to find the thing that killed her." He had told Dean. "I'm going to kill it with my bare hands when I have half the chance."

Dean had grabbed his shoulder and squeezed, but he hadn't said anything.

Such was the brotherly love.

Sam ached for Jess' soft touch, her kiss, her laugh.

He knelt down in front of her grave and pressed his hand to his mouth, as if that would stop the sobs from racking his whole body.

"I'm sorry." He whispered. "I'm sorry, but I have to. I have to kill it, you have to be avenged, Jess. My love."

**WOW. WHAT AM I DOING? THAT WAS SAD. THIS WAS SUPPOSED TO BE A FUNNY FIC. Sorry…. **


End file.
